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Top 10 Most Lopsided Trade Deadline Deals in NHL History

The trade deadline is one of the busiest times of the year for NHL general managers, and the deals that get made throughout the league on that day tend to have an emphasis on risk and reward. In this top 10 list, we will analyze the deals that have gone down on deadline day in years past that turned out to be pretty rewarding for some teams, but were risks that backfired for others.

Some of these trades involved superstars being dealt in trades that saw pieces coming back who proved to be insignificant. Other deals involved players who wouldn’t have necessarily wowed fans at the time, but ended up being key elements of Stanley Cup-winning teams that same season.

One trade involves players that would win a Stanley Cup with their new team for two consecutive seasons, another involves a longtime fan favourite leaving their club, and another involves a player who would go to a new club for a huge contract that has since led to repercussions for the team who acquired him: they have been forced to use the 30th overall pick in this year’s draft as punishment for circumventing the salary cap, after the initial punishment was forfeiting their draft pick entirely.

Although several of these trades didn’t seem like blockbusters at the time, they way they ended up developing in subsequent seasons proved to be a boon for some teams and a rather regrettable bust for others. Sadly for some GMs, they have made the mistake of trading eventual superstar players before they could truly blossom. You never know what the end result of that kind of trade could be, and that’s the beauty of the trade deadline. Let’s take a look at the top 10 most lopsided deals in NHL trade deadline history.

For the most part, this trade makes this list because of how it blew up in New Jersey’s face after all was said and done. While Ilya Kovalchuk was once one of the NHL’s premier snipers, he would eventually return to Russia to compete in the KHL with SKA Saint Petersburg after just a few seasons in New Jersey and with 12 years and $77 million left on his contract. As for Oduya, he played for the Thrashers even after they had become the Winnipeg Jets in 2011, and now plies his trade in Chicago where he won a Stanley Cup last season.

Seeing the player known as “Captain Canada” leave the Oilers sent shockwaves across the league, but Ryan Smyth was traded to the New York Islanders in 2007 after 12 seasons in Edmonton. His stint at the Nassau Coliseum proved to be brief, but he helped the Islanders squeeze into the eighth and final seed of the Eastern Conference for the playoffs that year. Smyth would play for the Avalanche and the Kings before returning to the Oilers in 2011. O’Marra would only play 33 games in the NHL and now plies his trade in Norway, while Nilsson and Plante play in Russia and Austria respectively.

8 Penguins receive James Neal and Matt Niskanen from Stars for Alex Goligoski

Kelvin Kuo/USA TODAY Sports Images

After both Neal and Goligoski were having disappointing seasons points-wise for Dallas in 2010-11, Stars general manager Joe Nieuwendyk sent both of them to the Penguins in return for Alex Goligoski. Neal would find his groove on a line with Evgeni Malkin, scoring 81 points in 2011-12 while Sidney Crosby was out injured for much of the season. Niskanen has seen his point production rise considerably in Pittsburgh, as he’s already enjoying a career season with the Pens this year. Goligoski is still a consistent 30 point-producing defenseman in Dallas, but Niskanen is having a better season. With Neal part of the equation, it’s clear this deal was a victory for the Penguins.

Miroslav Satan’s first two years in the NHL did not result in particularly prolific seasons for the Oilers, thus then-Oilers GM Glen Sather probably saw him as expendable, and traded the Slovak right winger to Buffalo for Craig Millar and Barrie Moore on deadline day in 1997. The deal ended up having more repercussions for the Oilers than they’d initially thought: Satan would enjoy eight fruitful seasons with the Sabres, peaking with a 75-point season in 2002-03, and a 37-goal season the year before. Millar and Moore would play 40 games between them for the Oilers. Millar retired in 2002, while Moore plays his club hockey in England.

After the Tampa Bay Lightning signed Brad Richards to a $39 million contract spanning five years, it became increasingly difficult for the team to hang on to him. Three hours before deadline day in 2008, the Lightning decided to ship Richards and goalie Johan Holmqvist to Dallas in exchange for Mike Smith, Jussi Jokinen, Jeff Halpern and a fourth-round pick in 2009. Richards would spend the next few seasons producing great numbers offensively, even matching his 91-point total from 2005-06 in the 2009-10 season. Smith would play consistently for Tampa the next few seasons, but found greater success in Phoenix. Jokinen would play for Carolina and Pittsburgh after the trade, and Halpern is now in Phoenix after bouncing around multiple teams following the Richards deal.

Although Marian Hossa was putting up career-high point totals with the Atlanta Thrashers, the team remained one of the worst in the league, and he was dealt on deadline day in 2008 to Pittsburgh with Pascal Dupuis for Colby Armstrong, Erik Christensen, Angelo Esposito and a first-round pick. Hossa would fall just short in his attempt to win the Cup in Pittsburgh – and also fell short the next year in Detroit – but ended up winning two in Chicago. Dupuis has seen his point totals rise in a big way alongside Sidney Crosby. None of the pieces traded to the Thrashers are still with the team now based in Winnipeg.

4 Canucks receive Markus Naslund from Penguins for Alek Stojanov

The former NHL superstar known as “Nazzy” started his career off only finding his groove in his third season with the Pittsburgh Penguins in 1995-96, during which he was traded on deadline day to the Canucks for then-prospect Alek Stojanov. Naslund would go on to have 12 fantastic seasons in Vancouver – two-thirds of which were spent as team captain – and reached his height in 2002-03 with 104 points on the season, eventually having the Canucks retire his #19. Stojanov, on the other hand, scored only seven points in 107 NHL games despite being drafted seventh overall in 1991.

One of the Kings’ marquee players during the ‘70s, Butch Goring would get traded at the deadline in 1980 to the New York Islanders for Billy Harris and Dave Lewis. Already a winner of the Bill Masterton and Lady Byng trophies, Goring would go on to become one of the major building blocks of the New York Islanders’ four consecutive Stanley Cup wins between 1980 and 1983. As for Harris, he would struggle to replicate his Islanders point totals while playing for the Kings and later the Leafs. Lewis would play the next few seasons as a King, but was hardly a star player and is better known as an assistant coach nowadays for the Carolina Hurricanes.

As a Calgary Flame, Brett Hull was better known as Bobby Hull’s son up until having his breakout season in 1987-88. However, the Flames traded Hull and Steve Bozek to the St. Louis Blues for Rob Ramage and Rick Wamsley. This would be the start of 11 extremely successful seasons in St. Louis for Hull, who went on to be the Blues’ top player despite Calgary winning the Stanley Cup the following season. However, Hull would one-up the Flames by winning in 1999 and 2002 with Dallas and Detroit respectively. Neither Ramage nor Wamsley would play particularly significant roles in Calgary, despite both players winning a Cup with the Flames in 1989.

Arguably the most underrated player in NHL history, Ron Francis hadn’t had much experience in the playoffs with the Whalers despite his high point totals each season. In March of 1991, Francis was traded with Ulf Samuelsson and Grant Jennings to the Penguins for John Cullen, Jeff Parker and Zarley Zalapski. The trade for Francis, Samuelsson and Jennings paid off, as all three won the Stanley Cup that year in Pittsburgh and again the following season. Parker only played four games with the Whalers, Cullen would play one successful season in 1992 in Hartford before going to Toronto the following season, and Zalapski’s career peaked with the Whalers before going to the Calgary Flames in 1993.